1-((Z)-(naphthalene-4-ylimino)methyl)-naphthalene-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-((Z)-(naphthalene-4-ylimino)methyl)-naphthalene-2-ol
• 英文别名: (E)-1-((naphthalen-1-ylimino)methyl)naphthalen-2-ol；N-(α-Naphthyl)-2-oxy-1-naphthaldimine；2-hydroxynaphthylidene-1'-naphthylamine
• 化学式: C₂₁H₁₅NO
• 分子量: 297.356
• InChiKey: CFVMLACBKWKHEP-HYARGMPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tris(triphenylphosphine)ruthenium(II) chloride 、 1-((Z)-(naphthalene-4-ylimino)methyl)-naphthalene-2-ol 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以74.23%的产率得到
  参考文献：
  名称：

  一氧化二氮与衍生自双齿配体的钌配合物的反应性：钌亚硝酰基配合物的结构，光诱导生成和估算一氧化氮†

  摘要：

  钌配合物[Ru（L 1）（PPh 3）2（CO）Cl]（1）[其中L 1 H为（E）-2-（（萘-1-亚氨基）甲基）苯酚]和[Ru（L 2）（PPh 3）2（CO）Cl]（2）[其中L 2 H是（E）-1-（（萘-1-ylimino）甲基）萘-2-醇] [H表示可解离质子]通过UV-Vis，IR和NMR光谱研究合成并表征。一氧化氮反应活性研究提供了钌亚硝酰基络合物[Ru（L 1）（PPh 3）（NO 2）（NO）Cl]（1a）和[Ru（L 2）（PPh 3）（NO 2）（NO）Cl]（2a）分别来自络合物1和2。配合物1a和2a通过不同的光谱学研究进行了表征。配合物2a的分子结构通过X射线晶体学测定。通过循环伏安法研究了所有配合物的氧化还原性质。发现配位的一氧化氮是光不稳定的，并且通过还原的肌红蛋白捕获了光生NO，并且通过Griess反应估计了释放的NO。

  DOI：

  10.1039/c4ra04767b
• 作为产物：
  描述：

  1-萘胺 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 生成 1-((Z)-(naphthalene-4-ylimino)methyl)-naphthalene-2-ol
  参考文献：
  名称：

  两种结构相关的席夫碱的酮-烯醇互变异构现象：激发的酮互变异构体的直接和间接产生方式

  摘要：

  飞秒时间分辨的两个结构相关的，内部氢键的席夫碱的吸收光谱已报道。作为烯醇互变异构体稳定的2-羟基萘-1'-萘胺（HNAN）经历超快激发态分子内质子转移，而作为酮结构稳定的2-羟基萘-（8'-氨基喹啉）（HNAQ）表现出不同寻常电子激发后的弛豫路径。尤其是，发现了特征时间约为700 fs的漂白带上升，并归因于S 1荧光态从“热”激发态逐渐扩散。伴随TDDFT计算的结果被用于构建激发的HNAQ分子的弛豫路线图。

  DOI：

  10.1016/j.cplett.2005.09.069

文献信息

• Naphthalene based highly selective OFF–ON–OFF type fluorescent probe for Al3+ and NO2− ions for living cell imaging at physiological pH
  作者：Animesh Sahana、Arnab Banerjee、Sisir Lohar、Sudipta Das、Ipsit Hauli、Subhra Kanti Mukhopadhyay、Jesús Sanmartín Matalobos、Debasis Das

  DOI：10.1016/j.ica.2012.12.012

  日期：2013.3

  A naphthalene based fluorescent probe, 1-((Z)-(naphthalene-4-ylimino) methyl) naphthalene-2-ol (L) has been synthesized by condensing 1-naphthyl amine with 2-hydroxy naphthaldehyde. The structure of L has been established by single crystal X-ray structure. It selectively binds Al3+ with a binding constant (K-a) of 1.83 x 10(5) M (1/2) and detection limit of 1.0 x 10 (7) M. Moreover, [L-Al3+] complex can detect NO2 ion as low as 5.7 x 10 (8) M. Binding of L to Al3+ and [L-Al3+] complex to NO2 ion has been established by different spectroscopic studies. The probe is very effective for detection of intracellular Al3+ through fluorescence microscopic imaging. (C) 2012 Elsevier B.V. All rights reserved.
• Intramolecular N−H...O hydrogen bonding, quinoid effect, and partial π-electron delocalization in N-aryl Schiff bases of 2-hydroxy-1-naphthaldehyde: the crystal structures of planar N-(α-naphthyl)- and N-(β-naphthyl)-2-oxy-1-naphthaldimine
  作者：Marijana Gavranić、Branko Kaitner、Ernest Meštrović

  DOI：10.1007/bf02018692

  日期：1996.1

  The structures of N-(alpha-naphthyl)-2-oxy-1-naphthaldimine 1 and N-(beta-naphthyl)-2-oxy-1-naphthhaldimine 2 have been investigated by X-ray analysis and by spectroscopic methods. Crystals of 1 are monoclinic, space group Pn, with cell dimensions a = 10.823(3), b = 5.826(2), c = 11.899 (3) Angstrom, and beta = 99.66(3)degrees. Compound 2 crystallizes in the orthorhombic space group Pca2(1) with a = 17.564(3), b = 6.314(2), and c = 13.663(4) Angstrom. The IR spectra exhibited neither N-H nor O-H stretching frequencies. The existence of the intramolecular hydrogen bonding of N-H O type was predicted by spectroscopic experiment but unequivocally established by diffraction experiment in both cases 1 and 2. The molecules 1 and 2 are significantly planar with considerable quinoid effect at the 2-oxy-naphthaldimine moiety. Although essentially planar, both molecules 1 and 2 show the delocalization of pi-electrons only in the central part of the molecules including C=N imino group with pendent ring carbon atoms. Intermolecular attractions in the crystals belong to weak van der Waals interactions between discrete planar molecules spatially arranged into the expected herringbone motif in the solid state.